CN102574951A - (meth)acrylic resin composition - Google Patents
(meth)acrylic resin composition Download PDFInfo
- Publication number
- CN102574951A CN102574951A CN2010800478210A CN201080047821A CN102574951A CN 102574951 A CN102574951 A CN 102574951A CN 2010800478210 A CN2010800478210 A CN 2010800478210A CN 201080047821 A CN201080047821 A CN 201080047821A CN 102574951 A CN102574951 A CN 102574951A
- Authority
- CN
- China
- Prior art keywords
- methyl
- propenoate
- acrylic resin
- resin compsn
- adherend
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 55
- 229920000178 Acrylic resin Polymers 0.000 title claims abstract description 55
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 238000010438 heat treatment Methods 0.000 claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 239000000853 adhesive Substances 0.000 claims abstract description 9
- 230000001070 adhesive effect Effects 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 87
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 46
- 238000012986 modification Methods 0.000 claims description 23
- 230000004048 modification Effects 0.000 claims description 23
- 230000007704 transition Effects 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 14
- 229910052753 mercury Inorganic materials 0.000 claims description 14
- -1 3-adamantyl dimethanol Chemical compound 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 229940059574 pentaerithrityl Drugs 0.000 claims description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052724 xenon Inorganic materials 0.000 claims description 9
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 7
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 238000005286 illumination Methods 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 5
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- 229910001507 metal halide Inorganic materials 0.000 claims description 4
- 150000005309 metal halides Chemical class 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 2
- 230000009477 glass transition Effects 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 48
- 239000011521 glass Substances 0.000 description 19
- 230000003287 optical effect Effects 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 6
- 239000002390 adhesive tape Substances 0.000 description 5
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000003522 acrylic cement Substances 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 3
- 230000001464 adherent effect Effects 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000005476 soldering Methods 0.000 description 3
- FIOCEWASVZHBTK-UHFFFAOYSA-N 2-[2-(2-oxo-2-phenylacetyl)oxyethoxy]ethyl 2-oxo-2-phenylacetate Chemical compound C=1C=CC=CC=1C(=O)C(=O)OCCOCCOC(=O)C(=O)C1=CC=CC=C1 FIOCEWASVZHBTK-UHFFFAOYSA-N 0.000 description 2
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- YOQPJXKVVLAWRU-UHFFFAOYSA-N ethyl carbamate;methyl prop-2-enoate Chemical compound CCOC(N)=O.COC(=O)C=C YOQPJXKVVLAWRU-UHFFFAOYSA-N 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 238000012797 qualification Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical group 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- LDDRLENOECTLGT-UHFFFAOYSA-N C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.OC(C(C)O)C Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.OC(C(C)O)C LDDRLENOECTLGT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000511976 Hoya Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- PSGCQDPCAWOCSH-BREBYQMCSA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C=C)C[C@@H]1C2(C)C PSGCQDPCAWOCSH-BREBYQMCSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 229920006222 acrylic ester polymer Polymers 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/20—Esters of polyhydric alcohols or polyhydric phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2433/00—Presence of (meth)acrylic polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T156/00—Adhesive bonding and miscellaneous chemical manufacture
- Y10T156/11—Methods of delaminating, per se; i.e., separating at bonding face
- Y10T156/1153—Temperature change for delamination [e.g., heating during delaminating, etc.]
- Y10T156/1158—Electromagnetic radiation applied to work for delamination [e.g., microwave, uv, ir, etc.]
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Abstract
Disclosed is an adhesive (meth)acrylic resin composition which has high adhesion properties, enables the production of an adhered material that can be used at temperatures as high as 250 DEG C or higher, and has low outgas properties and heat resistance. Specifically disclosed is a (meth)acrylic resin composition which comprises (A) a polyfunctional (meth)acrylate and (B) a photopolymerization initiator that has a mass loss under heating of 15 mass% or less when heated from 30 DEG C to 250 DEG C at a temperature increase rate of 10 DEG C/min under a nitrogen stream, wherein a cured product of the composition has a glass transition temperature of 250 DEG C or higher.
Description
Technical field
The present invention relates to a kind of (methyl) acrylic resin compsn.
Background technology
In the past, the Photocurable resin compositions such as ultra-violet solidified or visible-light curing property that use in the manufacturing of various electronic units, optics, optical device more.Variety of ways such as that employed mode has is bonding, perfusion, coating, sealing, moulding.Employed compsn is known to have (methyl) acrylic acid series, epoxy system, trimethylene oxide system, polyethylene-based, polyenoid/polythiol system etc.Particularly (methyl) acrylic acid series is with the most use, uses urethane acrylate system, epoxy acrylate system, polyester acrylate system etc. according to purposes.In addition, when being only limited to the joint of optics, optical device, (methyl) acrylic acid series such as urethane acrylate system and polyenoid/polythiol are with the most use.
But; In recent years; In the multifunction progress of optics, optical device, the performance that Photocurable resin composition is asked to reach, quality are also of all kinds and require high level gradually, and Photocurable resin composition in the past becomes gradually and lacks perfection.Therefore, just carrying out various researchs now.As the desired performance of Photocurable resin composition, quality, particularly, can enumerate the viscosity that conforms to purposes, low foul smell, low outgas, high transparent, high adhesion, high heat resistance etc.
In recent years, the thermotolerance in the time of particularly can enumerating production as necessary performance.For example, sometimes among the surface treatment of optics, optical device, part application etc., implement to surpass vapor deposition treatment or the baking application under the enforcement high temperature down of 200 ℃ of high temperature.In addition, except IC or resistance, inductor block etc. the electronic unit, nowadays the surface-assembled of optical device such as image sensor on also can the applicable circuit substrate at this moment, can be passed through the pyritous Reflow Soldering.In recent years, unleaded along with scolder particularly, it is strict that the temperature condition of Reflow Soldering also becomes gradually.In this production process, in order to improve the quality of optics, optical device, or boost productivity, manufacture a finished product rate, require the use position of Photocurable resin composition can stand high-temperature heating treatment fully.That is, need in high-temperature heating treatment, not produce peel off, foaming, crack, variable color etc.
In addition, sometimes because the outgas that produces during above-mentioned high-temperature heating treatment and the locality of generation part, equipment is polluted, or because the operation after making, the outgas that produced when using make parts, device characteristics decline.Particularly along with in recent years optics, the miniaturized of optical device, precise treatment, the problem that outgas causes characteristic the to descend more and more significant that becomes.
In view of this present situation; Though disclose a kind of acrylic adhesive with light-cured type of thermotolerance, low air release property; It still can't say the thermotolerance of the acrylic adhesive of this light-cured type, low air release property all abundant (with reference to patent documentation 1) by formations such as polyhutadiene compound, simple function (methyl) propenoate with alicyclic group or chain fatty group, simple function (methyl) propenoate with hydroxyl and/or ring-type ehter bond and simple function acrylamide compounds.
In addition, as the thermotolerance tackiness agent, disclosing the excellent polyimide of a kind of peel adhesion strength is tackiness agent, but owing to be heating and curing, thus solidify time-consuming, productivity poor (with reference to patent documentation 2).
And then; A kind of stable on heating acrylic adhesive that has of two liquid host types is disclosed; Wherein contain methylacrylic acid, (methyl) IBOA, reach the aqueous rubber that has the polymerizability unsaturated double-bond endways, but can't say thermotolerance, low air release property all abundant (with reference to patent documentation 3).
In addition; A kind of acrylic adhesive is disclosed; It is characterized in that; As various adherends being had same high bond strength; And thermotolerance and wet fastness are good, rigidity also excellence and low, the bonding energy line curing resin composition that should diminish of cure shrinkage property, contain molecular weight and be (methyl) propenoate of 500～5000, being situated between is had simple function (methyl) propenoate, (methyl) propenoate of hydroxyl, polyfunctionality (methyl) propenoate, Photoepolymerizationinitiater initiater, the inhibitor of the unsaturated alkyl of carbon number 2～8 by ester bond.Said molecular weight is that the main chain backbone of (methyl) propenoate of 500～5000 is at least a kind that is selected from polyhutadiene, TR 301 and their hydrogenate, and has at least 1 (methyl) acryl at the end or the side chain of this main chain backbone; But about not record (with reference to patent documentation 4) of thermotolerance.
And, a kind of adhesive composition is also disclosed, it is characterized in that, contain multifunctional (methyl) propenoate, simple function (methyl) propenoate, Photoepolymerizationinitiater initiater, and be-50 ℃～40 ℃ by the second-order transition temperature of the resulting cured body of above-mentioned compsn.But obtain the not record (with reference to patent documentation 5) of sufficient thermotolerance about the second-order transition temperature that improves cured body.
Patent documentation 1: TOHKEMY 2006-342222 communique
Patent documentation 2: No. 3014526 communique of Japanese Patent
Patent documentation 3: No. 3934701 communique of Japanese Patent
Patent documentation 4: No. 2006/129678 pph of International Publication
Patent documentation 5: No. 2008/018252 pph of International Publication
Summary of the invention
In order to solve the problem that these technological in the past problem, especially thermotolerances and air release property improve, through various researchs, the result has accomplished the present invention.
Promptly; One aspect of the present invention is a kind of (methyl) acrylic resin compsn; Wherein, contain (A) multifunctional (methyl) propenoate, (B) Photoepolymerizationinitiater initiater, should (B) Photoepolymerizationinitiater initiater under nitrogen gas stream with 10 ℃/minute of heat-up rates when 30 ℃ are warming up to 250 ℃; The heating quality decrement is below the 15 quality %, and the second-order transition temperature of the cured body that is obtained by said composition is more than 250 ℃.
In a kind of embodiment of (methyl) of the present invention acrylic resin compsn, (A) multifunctional (methyl) propenoate accounts for more than the 90 quality % in (methyl) acrylic resin compsn.
In a kind of embodiment of (methyl) of the present invention acrylic resin compsn, under helium flow, will be below the 6 quality % by the heating quality decrement of the resulting cured body of (methyl) acrylic resin compsn when placing 10 minutes for 300 ℃.
In a kind of embodiment of (methyl) of the present invention acrylic resin compsn,, contain (B) Photoepolymerizationinitiater initiater of 0.01～5 mass parts with respect to (A) of 100 mass parts multifunctional (methyl) propenoate.
In a kind of embodiment of (methyl) of the present invention acrylic resin compsn; (B) Photoepolymerizationinitiater initiater is for being selected from 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propionyl group)-benzyl]-phenyl }-2-methyl-propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1,2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholine-4-base-phenyl)-butane-1-ketone, two (2; 4; The 6-trimethylbenzoyl) phenyl phosphine oxide, 2; 4, in 6-trimethylbenzoyl diphenyl phosphine oxide, phenylor-acetate-2-[2-oxygen-2-phenyl-acetoxyl group-oxyethyl group]-ethyl ester, phenylor-acetate 2-[2-hydroxyl-oxyethyl group]-ethyl ester more than a kind.
In a kind of embodiment of (methyl) of the present invention acrylic resin compsn; (A) multifunctional (methyl) propenoate is for being selected from 1; 3-adamantyl dimethanol two (methyl) propenoate, trimethylolpropane tris (methyl) propenoate, isocyanuric acid oxyethane modification two (methyl) propenoate, isocyanuric acid oxyethane modification three (methyl) propenoate, tetramethylolmethane three (methyl) propenoate, tetramethylolmethane four (methyl) propenoate, dihydroxy methylpropane four (methyl) propenoate, Dipentaerythritol five (methyl) propenoate, Dipentaerythritol six (methyl) propenoate, 1, in 2-polyhutadiene terminal amino group manthanoate (methyl) propenoate more than a kind.
In a kind of embodiment of (methyl) of the present invention acrylic resin compsn, contain (C) polymerization retarder.
The present invention is a kind of tackiness agent on the other hand, wherein, comprises (methyl) of the present invention acrylic resin compsn.
The present invention is a kind of method of manufacture of adherend on the other hand, wherein, comprising: use tackiness agent of the present invention that base material is fitted, and to this tackiness agent irradiation visible rays or ultraviolet and base material is bonded to each other.
The present invention is a kind of method of use of adherend on the other hand, wherein, comprising: use tackiness agent of the present invention with base material fit each other, bonding after, resulting adherend is used in the environment more than 250 ℃.
The present invention is a kind of disassembling method of adherend on the other hand, wherein, comprising: on one side to utilizing the adherend that forms after the tackiness agent adhesive substrate of the present invention to be heated to more than 150 ℃, Yi Bian the above light of illumination wavelength 280nm.
In the method for use of adherend of the present invention in one embodiment, radiation source is selected from high voltage mercury lamp, ultrahigh pressure mercury lamp, metal halide lamp, xenon lamp and encloses the photoflash lamp of xenon.
Use (methyl) of the present invention acrylic resin compsn, can access thermotolerance and low air release property excellent in curing thing.
Embodiment
As (A) multifunctional (methyl) propenoate, can use at polymkeric substance (comprising oligopolymer and superpolymer) end or polymkeric substance (comprising oligopolymer and superpolymer) side chain to have multifunctional (methyl) acrylic ester polymer (comprising oligopolymer and superpolymer) of (methyl) acryl more than 2 or have the monomer of (methyl) acryl more than 2.So long as the second-order transition temperature of cured body is more than 250 ℃; Then employed (A) multifunctional (methyl) acrylic ester is not special to be limited; In the present invention; Because the kind of the second-order transition temperature of the cured body of resin combination receives multifunctional (methyl) propenoate and content domination thereof in order to control it as more than 250 ℃, are preferably used multifunctional (methyl) propenoate of specified quantitative.In typical embodiment of the present invention; Multifunctional (methyl) propenoate can account for more than the 90 quality % in (methyl) acrylic resin compsn; In more typical embodiment, can account for more than the 95 quality %, for example can occupy 90～99 quality %.
In the present invention, because the domination of the kind of the second-order transition temperature of the cured body of resin combination also receives multifunctional (methyl) propenoate in order to control it as more than 250 ℃, is preferably used multifunctional (methyl) propenoate of special component.
As monomeric multifunctional (methyl) propenoate; Can enumerate 1,3-adamantyl dimethanol two (methyl) propenoate, trimethylolpropane tris (methyl) propenoate, isocyanuric acid oxyethane modification two (methyl) propenoate, isocyanuric acid oxyethane modification three (methyl) propenoate, tetramethylolmethane three (methyl) propenoate, tetramethylolmethane four (methyl) propenoate, dihydroxy methylpropane four (methyl) propenoate, Dipentaerythritol five (methyl) propenoate, Dipentaerythritol six (methyl) propenoate etc.Can use in them more than a kind or 2 kinds.
Multifunctional (methyl) propenoate as polymkeric substance; Can enumerate 1; 2-polyhutadiene terminal amino group manthanoate (methyl) propenoate (for example Japanese Cao Da corporate system " TE-2000 ", " TEA-1000 "), above-mentioned hydrogenate (for example Japanese Cao Da corporate system " TEAI-1000 "), 1 terminal amino group manthanoate (methyl) propenoate (for example Osaka organic chemistry corporate system " BAC-45 "), terminal (methyl) propenoate of TR 301, polyester urethane (methyl) propenoate (for example Japanese Synesis Company system " UV-2000B ", " UV-3000B ", " UV-7000B "), root are attend industrial's system " KHP-11 ", " KHP-17 ", polyester urethane (methyl) propenoate (for example Japanese Synesis Company system " UV-3700B ", " UV-6100B "), two A type epoxies (methyl) propenoate etc.Can use in these more than a kind or 2 kinds.
In multifunctional (methyl) propenoate; With regard to thermotolerance and low air release property; Preferred 1; 3-adamantyl dimethanol two (methyl) propenoate, trimethylolpropane tris (methyl) propenoate, isocyanuric acid oxyethane modification two (methyl) propenoate, isocyanuric acid oxyethane modification three (methyl) propenoate, tetramethylolmethane three (methyl) propenoate, tetramethylolmethane four (methyl) propenoate, dihydroxy methylpropane four (methyl) propenoate, Dipentaerythritol five (methyl) propenoate, Dipentaerythritol six (methyl) propenoate, 1, in 2-polyhutadiene terminal amino group manthanoate (methyl) propenoate more than a kind.Wherein, With regard to thermotolerance and low air release property; Preferred 1; In 3-adamantyl dimethanol two (methyl) propenoate, tetramethylolmethane three (methyl) propenoate, trimethylolpropane tris (methyl) propenoate, isocyanuric acid oxyethane modification (methyl) propenoate, isocyanuric acid oxyethane modification three (methyl) propenoate more than a kind; More preferably in trimethylolpropane tris (methyl) propenoate, isocyanuric acid oxyethane modification two (methyl) propenoate, isocyanuric acid oxyethane modification three (methyl) propenoate more than a kind, most preferably the mixture with (A-1) trimethylolpropane tris (methyl) propenoate, (A-2) isocyanuric acid oxyethane modification two (methyl) propenoate and isocyanuric acid oxyethane modification three (methyl) propenoate uses.
(A-2) containing ratio of isocyanuric acid oxyethane modification two (methyl) propenoate in the mixture of isocyanuric acid oxyethane modification two (methyl) propenoate and isocyanuric acid oxyethane modification three (methyl) propenoate is preferably 20～50 quality %, more preferably 30～40 quality %.(A-1) with (A-2) and with ratio preferred by quality ratio (A-1): (A-2)=3～70: 97～30, more preferably 5～15: 95～85.
With regard to thermotolerance and low air release property; (B) Photoepolymerizationinitiater initiater that uses in the present invention under nitrogen gas stream and heat-up rate be 10 ℃/minute when 30 ℃ are warming up to 250 ℃; Preferred dosage caloic decrement is below the 15 quality %, more preferably below the 8 quality %, most preferably below the 6 quality %.Based on reason economically, the heating quality decrement is preferably more than the 0.1 quality %, more preferably more than the 4 quality %.
As (B) Photoepolymerizationinitiater initiater; Can enumerate 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propionyl group)-benzyl]-phenyl }-2-methyl-propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1,2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholine-4-base-phenyl)-butane-1-ketone, two (2; 4; The 6-trimethylbenzoyl) phenyl phosphine oxide, 2; 4,6-trimethylbenzoyl diphenyl phosphine oxide, phenylor-acetate-2-[2-oxygen-2-phenyl-acetoxyl group-oxyethyl group]-ethyl ester, phenylor-acetate 2-[2-hydroxyl-oxyethyl group]-ethyl ester.Can use in them more than a kind or 2 kinds.
Wherein, With regard to thermotolerance and low air release property; Preferred 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propionyl group)-benzyl]-phenyl }-2-methyl-propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1,2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholine-4-base-phenyl)-butane-1-ketone, two (2,4, the 6-trimethylbenzoyl) phenyl phosphine oxide, 2; 4; In 6-trimethylbenzoyl diphenyl phosphine oxide, phenylor-acetate-2-[2-oxygen-2-phenyl-acetoxyl group-oxyethyl group]-ethyl ester, phenylor-acetate 2-[2-hydroxyl-oxyethyl group]-ethyl ester more than a kind, more preferably 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1,2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholine-4-base-phenyl)-butane-1-ketone, two (2,4; The 6-trimethylbenzoyl) phenyl phosphine oxide, 2; 4, in the 6-trimethylbenzoyl diphenyl phosphine oxide more than a kind, most preferably two (2; 4, the 6-trimethylbenzoyl) phenyl phosphine oxide.
In addition; The rate of mass reduction of the Photoepolymerizationinitiater initiater that above-mentioned heating causes; For example can use the thermal mass analytical equipment and under nitrogen gas stream, with 10 ℃/minute heat-up rates; Photoepolymerizationinitiater initiater when 30 ℃ are warming up to 250 ℃, with respect to the quality of the Photoepolymerizationinitiater initiater 30 ℃ the time, is represented with the rate of mass reduction (quality %) 250 ℃ the time.
Rate of mass reduction from the resulting cured body of (methyl) of the present invention acrylic resin compsn; For example can use the thermal mass analytical equipment; Under helium flow; The cured body that will be somebody's turn to do (methyl) acrylic resin compsn exposed to the open air 300 ℃ temperature in the time of 10 minutes, and with respect to the quality of the cured body before exposing to the open air, (quality %) representes with the rate of mass reduction after exposing to the open air.
Consider from low air release property, stable on heating viewpoint; Rate of mass reduction by the resulting cured body of (methyl) of the present invention acrylic resin compsn is preferably below the 6 quality %; More preferably below the 5 quality %; Most preferably being below the 4 quality %, more preferably below the 2 quality %, for example is 0.1～6 quality % further.
By the resulting cured body of (methyl) of the present invention acrylic resin compsn, can have the second-order transition temperature more than 250 ℃.On the other hand,, can't measure second-order transition temperature, so can the upper limit of second-order transition temperature be regarded as 400 ℃ greater than this temperature because (methyl) of the present invention acrylic resin compsn roughly can carry out thermolysis at 400 ℃.
In addition, the measuring method by the second-order transition temperature of the resulting cured body of (methyl) of the present invention acrylic resin compsn can use dynamic viscoelastic spectrum.In dynamic viscoelastic spectrum, can be to this cured body with certain heat-up rate stress application and strain, the temperature of summit (peak top) that will represent loss tangent (loss tangent) (below be abbreviated as tan δ) is as second-order transition temperature.Even if the low-down temperature from about-150 ℃ is warming up to certain temperature (Ta ℃) when also peak value not occurring; Can think that second-order transition temperature is below-150 ℃ or more than certain temperature (Ta ℃); But because the structure of (methyl) acrylic resin compsn; Its second-order transition temperature can not be for below-150 ℃, so can be used as more than certain temperature (Ta ℃).
(B) usage quantity of Photoepolymerizationinitiater initiater preferably contains (B) Photoepolymerizationinitiater initiater of 0.01～5 mass parts with respect to (A) multifunctional (methyl) propenoate 100 mass parts.The usage quantity of Photoepolymerizationinitiater initiater is 0.01 mass parts when above, can access sufficient solidified nature, when 5 mass parts are following, and low air release property and excellent heat resistance.With regard to solidified nature, low air release property and thermotolerance, be preferably 0.1～3 mass parts, more preferably 0.3～2 mass parts.
In the scope of not damaging the object of the invention, (methyl) of the present invention acrylic resin compsn can use simple function (methyl) propenoate.(methyl) of the present invention also can obtain good effect even if the acrylic resin compsn does not use simple function (methyl) propenoate.
In order to improve stability in storage, (methyl) of the present invention acrylic resin compsn can use (C) polymerization retarder.As polymerization retarder; Can enumerate toluhydroquinone, quinhydrones, 2; 2-methylene radical-two (4-methyl-6-tert butyl phenol), catechol, Hydroquinone monomethylether, a tertiary butylated hydroquinone, DBH 2,5 di tert butylhydroquinone, para benzoquinone, 2,5-phenylbenzene-para benzoquinone, 2; 5-di-t-butyl para benzoquinone, TNP, Hydrocerol A, thiodiphenylamine, tert-butyl catechol, 2-butyl-4-BHA and 2,6-di-t-butyl-p-cresol etc.Wherein, preferred 2,2-methylene radical-two (4-methyl-6-tert butyl phenol).
With respect to (A) of 100 mass parts, (C) usage quantity of polymerization retarder is preferably 0.001～3 mass parts, more preferably 0.01～2 mass parts.0.001 when mass parts is above, can guarantee stability in storage, when 3 mass parts are following, can access good binding property, do not have uncured situation yet.
In (methyl) of the present invention acrylic resin compsn, also can use polar organic solvent simultaneously.
In the scope of not damaging the object of the invention, (methyl) of the present invention acrylic resin compsn also can use additives such as various elastomericss such as acrylic rubber commonly used, urethanes, acrylonitrile-butadiene-styrene (ABS) rubber, mineral filler, solvent, extender, enhancing material, softening agent, tackifier, dyestuff, pigment, fire retardant, silane coupling agent and interfacial agent.
When using (methyl) of the present invention acrylic resin compsn to come adhesive substrate each other, preferably the energy at wavelength 365nm is 1～8000mJ/cm
2Scope irradiation visible light or ultraviolet ray.Energy is 1mJ/cm
2When above, can access sufficient binding property, 8000mJ/cm
2When following, productivity is excellent and be not easy to produce decomposition product from Photoepolymerizationinitiater initiater, and can suppress the generation of air release property.With regard to productivity, binding property, air release property, be preferably 100～4000mJ/cm
2Scope, 300～2000mJ/cm more preferably
2Scope.
Use (methyl) of the present invention acrylic resin compsn institute adherent base material, not special restriction, but preferred at least one side's base material is the transparent substrate of printing opacity.As transparent substrate, can enumerate the organic substrate of the inorganic substrate, plastics etc. of crystal, glass, quartz, Calcium Fluoride (Fluorspan) etc.Wherein, based on having versatility and can obtaining good result this reason, preferred glass and quartz.
In a kind of embodiment of (methyl) of the present invention acrylic resin compsn, can be that light-cured type and its cured body have excellent thermotolerance.In a kind of embodiment of (methyl) of the present invention acrylic resin compsn, even if expose to the open air at high temperature, release quantity is also few, is suitable for joint, sealing and the coating of various opticses or optical device, electronic unit.
The cured body of (methyl) of the present invention acrylic resin compsn can be preferably more than 200 ℃, more preferably more than 250 ℃, most preferably be in the high temperature more than 300 ℃ and use.The cured body of (methyl) of the present invention acrylic resin compsn can be preferably below 500 ℃, more preferably below 400 ℃, most preferably be below 350 ℃ and use.
And then the present invention in one embodiment; Can through will use adherend that the tackiness agent adhesive substrate forms while be heated to illumination wavelength more than 150 ℃ as more than the 280nm, typical wavelength is that light more than 300～400nm reduces its binding property, adherend is disintegrated.
The temperature of the adherend when disintegrating causes that from disintegration property and heating the viewpoint of base material deterioration considers preferred 150 ℃～300 ℃ scope, more preferably 180 ℃～290 ℃ scope, most preferably 200 ℃～280 ℃ scope.
In order to utilize the radiogenic heat of irradiates light, the light that a preferred side's not transmission of base material 280nm is above absorbs the light more than the 280nm through base material, can heat adherend effectively.
Disassembling method of the present invention is in one embodiment, from using the base material side of tackiness agent adherent adherend, with the light of the above wavelength of irradiation 280nm more than certain energy.In the time of accessing good separability, available hand is easily peeled off adherend.
Rayed energy during disintegration is with the preferred 1000～5000000mJ/cm of accumulative total light quantity of the light of wavelength 365nm
2, more preferably 10000～3000000mJ/cm
2, most preferably 28000～2000000.1000mJ/cm
2Disintegrate 5000000mJ/cm when above easily
2When following, the situation of productivity can not appear not having.
So long as emission wavelength is more than the 280nm, radiation source can be lamp source, LASER Light Source etc., not special the qualification.As radiation source, so long as deuterium lamp (deuterium lamp), mercury lamp (comprise and use 10
5The high voltage mercury lamp of the above mercury vapour of Pa, use 10
6The ultrahigh pressure mercury lamp of the above mercury vapour of Pa, use the low pressure mercury lamp of the following mercury vapour of 100Pa), known energy exposure sources such as xenon lamp, xenon-mercury reciprocally incorporated lamp, halogen lamp, Excimer lamp, indium lamp, thallium lamp, LED lamp, electrodeless discharge lamp, just can use.Wherein, consider the photoflash lamp of the high voltage mercury lamp that preferred irradiation energy is high, ultrahigh pressure mercury lamp, metal halide lamp, xenon lamp, inclosure xenon from the viewpoint of the disintegration property of adherend.
With the not special qualification of the method for adherend heating.As thermal source, can use hot plate or baking oven, also the radiogenic heat of irradiates light capable of using heats adherend.
[embodiment]
Below, can enumerate embodiment and comparative example illustrates in greater detail the present invention.But the present invention is not limited by these embodiment.
(embodiment 1)
Use Viscoat 295 (East Asia Synesis Company system " ARONIX M-309 " of 100 mass parts; Below be abbreviated as " M-309 ") as (A) multifunctional (methyl) propenoate; 2-dimethylamino-the 2-of 1 mass parts (4-methyl-benzyl)-1-(4-morpholine-4-base-phenyl)-butane-1-ketone (CIBA JAPAN corporate system " IRGACURE379 "; Below be abbreviated as " IRGACURE379 ") as (B) Photoepolymerizationinitiater initiater; 0.1 2 of mass parts; 2-methylene radical-two (4-methyl-6-tert butyl phenol) (Sumitomo Chemical Co. Ltd.'s system " SUMILIZER MDP-S " below is abbreviated as " MDP ") is made resin combination as (C) polymerization retarder.The result is as shown in table 1.
(evaluation method)
The second-order transition temperature of cured body (" second-order transition temperature " in the table): with (methyl) acrylic resin compsn of manufacturing, with the silicon chip of thickness 1mm as molding box and be clipped in the PET film.To be somebody's turn to do (methyl) acrylic resin compsn uses black lamp and is 500mJ/cm with the accumulative total light quantity of 365nm wavelength
2The condition of (" accumulative total light quantity " in the table), it is solidified after, and then be 500mJ/cm from following accumulative total light quantity with the 365nm wavelength
2Condition it is solidified, make thickness and be 1mm should (methyl) acrylic resin compsn cured body.The cured body of manufacturing is used cutting unit to cut off to become length 50mm, width 5mm and measures as second-order transition temperature and to use cured body.With resulting cured body; Use the Measurement of Dynamic Viscoelasticity device " DMS210 " of Seiko electronic industry manufactured; In nitrogen atmosphere, above-mentioned cured body applied the stress and the strain of the draw direction of 1Hz; And the limit is warming up to 250 ℃ of limits with the ratio of 2 ℃ of heat-up rate PMs from-150 ℃ and measures tan δ, and with summit (peak top) temperature of this tan δ as second-order transition temperature.The summit of tan δ is to be the peak in the zone more than 0.3 at tan δ.Tan δ is being 0.3 when following from-150 ℃ to 250 ℃ zone, and the summit of tan δ fixes on more than 250 ℃ and second-order transition temperature is decided to be more than 250 ℃.
The heating quality decrement of cured body (" the heating quality decrement of cured body " in the table):, be clipped in the PET film as partition with the backing plate (shim plate) of thickness 5 μ m with (methyl) acrylic resin compsn of manufacturing.To be somebody's turn to do (methyl) acrylic resin compsn uses black lamp and is 500mJ/cm with the accumulative total light quantity of 365nm wavelength
2Condition, it is solidified after, make thickness and be 5 μ m should (methyl) acrylic resin compsn cured body.With differential heat-thermal mass while determinator " TG-DTA2000SA " of the resulting cured body use of 10mg BRUKER AXS corporate system, under helium flow, placed 10 minutes at 300 ℃, measure the heating quality decrement of resulting cured body.To 300 ℃ of heat-up rates of placing 10 minutes be 10 ℃/minute.
The heating quality decrement of Photoepolymerizationinitiater initiater (" the heating quality decrement of Photoepolymerizationinitiater initiater " in the table): the differential heat-thermal mass while determinator " TG-DTA2000SA " that 10mg Photoepolymerizationinitiater initiater " IRGACURE379 " is used BRUKER AXS corporate system; Under nitrogen gas stream, be warming up to 250 ℃, measure the heating quality decrement of Photoepolymerizationinitiater initiater " IRGACURE379 " from 30 ℃ of heat-up rates with 10 ℃/minute.
Tensile shear bond strength (" bond strength " in the table): particularly; Use as the backboard glass (25mm * 25mm * thickness 0.5mm) that is glued material; Bond site is made as 25mm * 25mm; And the resin combination that the uses manufacturing 2 backboard glass of fitting, and through black lamp, be 500mJ/cm with the accumulative total light quantity of 365nm wavelength
2The condition of (" accumulative total light quantity " in the table) makes its curing, makes the test piece of tensile shear bond strength.The test piece of made is according to JISK6850 and use universal testing machine, is that 23 ℃, humidity are under 50% the environment in temperature, to measure the tensile shear bond strength in draw speed 10mm/ minute.
Tensile shear bond strength behind 250 ℃ of thermal tests (" 250 ℃ thermal test after bond strength " in the table): particularly; Use as the backboard glass (25mm * 25mm * thickness 0.5mm) that is glued material; Bond site is made as 25mm * 25mm; And the resin combination that the uses manufacturing 2 backboard glass of fitting, and through black lamp, be 500mJ/cm with the accumulative total light quantity of 365nm wavelength
2The condition of (" accumulative total light quantity " in the table) is solidified it, and makes test piece in 10 minutes in being heated to 250 ℃ baking oven, exposing to the open air.The test piece of made is according to JIS K6850 and use universal testing machine, is that 23 ℃, humidity are under 50% the environment in temperature, to measure the tensile shear bond strength in draw speed 10mm/ minute.
Tensile shear bond strength behind 300 ℃ of thermal tests (" 300 ℃ thermal test after bond strength " in the table): particularly; Use as the backboard glass (25mm * 25mm * thickness 0.5mm) that is glued material; Bond site is made as 25mm * 25mm; And the resin combination that the uses manufacturing 2 backboard glass of fitting, and through black lamp, be 500mJ/cm with the accumulative total light quantity of 365nm wavelength
2The condition of (" accumulative total light quantity " in the table) is solidified it, and makes test piece in 10 minutes in being heated to 300 ℃ baking oven, exposing to the open air.The test piece of made is according to JIS K6850 and use universal testing machine, is that 23 ℃, humidity are under 50% the environment in temperature, measures the tensile shear bond strength with draw speed 10mm/min.
Peel off-disintegrate test (1)
Make and the same test piece of above-mentioned tensile shear bond strength evaluation; After in being heated to 300 ℃ baking oven, exposing resulting test body to the open air 10 minutes, this test body is used high voltage mercury lamp (using appts: EYEGRAPHICS corporate system Eye Grandage ECS-401GX) and with the illumination 340mW/cm of 365nm wavelength from the backboard glass side
2And the condition with the represented accumulative total of table 1 light quantity is shone.Postradiation test piece uses universal testing machine under the environment of 23 ℃ of temperature, humidity 50% according to JIS K 6850, measures the tensile shear bond strength with draw speed 10mm/min.Peel off-disintegrate when test adherend top temperature through use the KAPTON adhesive tape with thermopair fit in light not a side's of direct irradiation backboard glass side measure.Mensuration and evaluation result are as shown in table 1.
Peel off-disintegrate test (2)
Make and the same test piece of above-mentioned tensile shear bond strength evaluation; After in being heated to 300 ℃ baking oven, exposing resulting test body to the open air 10 minutes, this test body is used metal halide lamp (using appts: EYEGRAPHICS corporate system Eye Grandage ECS-401GX) and with the illumination 340mW/cm of 365nm wavelength from the backboard glass side
2And the condition with the represented accumulative total of table 1 light quantity is shone.Postradiation test piece uses universal testing machine under the environment of 23 ℃ of temperature, humidity 50% according to JIS K 6850, measures the tensile shear bond strength with draw speed 10mm/min.Peel off-disintegrate when test adherend top temperature through use the KAPTON adhesive tape with thermopair fit in light not a side's of direct irradiation backboard glass side measure.Mensuration and evaluation result are as shown in table 1.
Peel off-disintegrate test (3)
Make and the same test piece of above-mentioned tensile shear bond strength evaluation; After in being heated to 300 ℃ baking oven, exposing resulting test body to the open air 10 minutes, this test body is used xenon-mercury lamp (using appts: HOYA corporate system EXECURE4000) and with the illumination 100mW/cm of 365nm wavelength from the backboard glass side
2And the condition with the represented accumulative total of table 1 light quantity is shone.In addition, from the backboard glass side temperature of hot plate being made as 200 ℃ heats.Postradiation test piece uses universal testing machine under the environment of 23 ℃ of temperature, humidity 50% according to JISK 6850, measures the tensile shear bond strength with draw speed 10mm/min.Peel off-disintegrate when test adherend top temperature through use the KAPTON adhesive tape with thermopair fit in light not a side's of direct irradiation backboard glass side measure.Mensuration and evaluation result are as shown in table 1.
Peel off-disintegrate test (4)
Make and the same test piece of above-mentioned tensile shear bond strength evaluation; After in being heated to 300 ℃ baking oven, exposing resulting test body to the open air 10 minutes, this test body is used the photoflash lamp of enclosing xenon (using appts: oxtail motor corporate system: FUV-201) and with the condition of the accumulative total light quantity of the wavelength of 365nm shown in the table 1 shine from the backboard glass side.Postradiation test piece uses universal testing machine under the environment of 23 ℃ of temperature, humidity 50% according to JIS K 6850, measures the tensile shear bond strength with draw speed 10mm/min.Peel off-disintegrate when test adherend top temperature through use the KAPTON adhesive tape with thermopair fit in light not a side's of direct irradiation backboard glass side measure.Mensuration and evaluation result are as shown in table 1.
Peel off-disintegrate test (5)
Make and the same test piece of above-mentioned tensile shear bond strength evaluation; After in being heated to 300 ℃ baking oven, exposing resulting test body to the open air 10 minutes, this test body is used xenon lamp (using appts: INFLIDGE industrial system: SBH-300A) and with from 6 of the distance irradiations of lamp 18.5mm respectively 10 seconds from the backboard glass side.Postradiation test piece uses universal testing machine under the environment of 23 ℃ of temperature, humidity 50% according to JIS K 6850, measures the tensile shear bond strength with draw speed 10mm/min.Peel off-disintegrate when test adherend top temperature through use the KAPTON adhesive tape with thermopair fit in light not direct irradiation one side's backboard glass side measure.Mensuration and evaluation result are as shown in table 1.
(embodiment 2～19, comparative example 1～4)
Except making the resin combination shown in table 1～5, likewise carry out with embodiment 1.The result is shown in table 1～5.
(materials used)
(composition A)
M-309: Viscoat 295 (East Asia Synesis Company system " ARONIX M-309 ")
A-201:1,3-adamantyl dimethanol diacrylate (the emerging product corporate system of bright dipping " ADAMANTATE A-201 ")
X-M-201:1,3-adamantyl dimethanol dimethacrylate (the emerging product corporate system of bright dipping " ADAMANTATE X-M-201 ")
TMP: trimethylolpropane trimethacrylate (chemical company of common prosperity society system " LIGHT-ESTER TMP ")
M-313: the mixture of isocyanuric acid oxyethane modification diacrylate and isocyanuric acid oxyethane modification triacrylate (containing ratio of isocyanuric acid oxyethane modification diacrylate is 30%～40%) (East Asia Synesis Company system " M-313 ")
M-315: the mixture of isocyanuric acid oxyethane modification diacrylate and isocyanuric acid oxyethane modification triacrylate (containing ratio of isocyanuric acid oxyethane modification diacrylate is 3%～13%) (East Asia Synesis Company system " M-315 ")
PE-3A: pentaerythritol triacrylate (chemical company of common prosperity society system " LIGHT-ACRYLATE PE-3A ")
PE-4A: tetramethylol methane tetraacrylate (chemical company of common prosperity society system " LIGHT-ACRYLATE PE-4A ")
M-408: dihydroxy methylpropane tetraacrylate (East Asia Synesis Company system " M-408 ")
M-400: the mixture of Dipentaerythritol five propenoate and dipentaerythritol acrylate (containing ratio of Dipentaerythritol five propenoate is 40%～50%) (East Asia Synesis Company system " M-400 ")
DPE-6A: dipentaerythritol acrylate (chemical company of common prosperity society system " LIGHT-ACRYLATE DPE-6A ")
TE-2000:1,2-polyhutadiene terminal amino group manthanoate methacrylic ester (Japanese Cao Da corporate system " TE-2000 ")
(composition B)
IRGACURE379:2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholine-4-base-phenyl)-butane-1-ketone (CIBA JAPAN corporate system " IRGACURE379 ")
IRGACURE127:2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propionyl group)-benzyl]-phenyl }-2-methyl-propane-1-ketone (CIBA JAPAN corporate system " IRGACURE127 ")
IRGACURE369:2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1 (CIBA JAPAN corporate system " IRGACURE369 ")
IRGACURE819: two (2,4, the 6-trimethylbenzoyl) phenyl phosphine oxides (CIBA JAPAN corporate system " IRGACURE819 ")
DAROCUR TPO:2,4,6-trimethylbenzoyl diphenyl phosphine oxide (CIBA JAPAN corporate system " DAROCUR TPO ")
IRGACURE754: the mixture (CIBA JAPAN corporate system " IRGACURE754 ") of phenylor-acetate-2-[2-oxygen-2-phenyl-acetoxyl group-oxyethyl group]-ethyl ester and phenylor-acetate 2-[2-hydroxyl-oxyethyl group]-ethyl ester
(composition C)
MDP:2,2-methylene radical-two (4-methyl-6-tert butyl phenol) (Sumitomo Chemical Co. Ltd.'s system " SUMILIZER MDP-S ")
Other
BDK: benzyl dimethyl ketal (CIBA SPECIALTY CHEMICALS corporate system " IRGACURE651 ")
IB-XA: IBOA (chemical company of common prosperity society system " LIGHT-ACRYLATE IB-XA ")
BZ: benzyl methacrylate (chemical company of common prosperity society system " LIGHT-ESTER BZ ")
1,6-HX-A:1,6-hexanediyl ester (chemical company of common prosperity society system " LIGHT-ACRYLATE 1,6-HX-A ")
[table 1]
[table 2]
[table 3]
[table 4]
[table 5]
Adhesive composition of the present invention can access thermotolerance and the big effect of binding property.Use between the adhesive composition of the present invention institute adherent base material, also can access the effect that binding property does not reduce even if use at the environment more than 250 ℃.Even if adhesive composition of the present invention 300 ℃ of exposures, also can access the few effect of outgas.
Utilize possibility on the industry
(methyl) of the present invention acrylic resin compsn is in the manufacturing of various electronic units, optics or optical device, because only need irradiation ultraviolet radiation or visible rays just to show strong binding property at an easy rate, so operation property, highly productive.(methyl) of the present invention though the cured body of acrylic resin compsn under 250 ℃ of such high temperature, not only binding property does not reduce, even and if under high temperature like this, release quantity is also few.Therefore, even if the various electronic units, optics or the optical device that use (methyl) of the present invention acrylic resin compsn to be bonded are also applicable when implementing to surpass the vapor deposition treatment under 200 ℃ of high temperature or implementing the baking application under the high temperature.
In addition, except IC, resistance, inductor block etc. the electronic unit, nowadays optical device such as image sensor also can be applicable to the surface-assembled on the circuit substrate, at this moment, and can be through the high temperature reflux weldering.In recent years, unleaded along with scolder particularly, it is strict that the temperature condition of Reflow Soldering also becomes gradually.In this production process, in order to improve the quality of optics or optical device, or boost productivity or manufacture a finished product rate, require the use position of Photocurable resin composition can stand high-temperature heating treatment fully.And use the optics or the optical device of the manufacturing of (methyl) of the present invention acrylic resin compsn, and can stand above-mentioned high-temperature heating treatment fully, therefore very useful on industry.
Claims (12)
1. (methyl) acrylic resin compsn; Wherein, Contain (A) multifunctional (methyl) propenoate, (B) Photoepolymerizationinitiater initiater; Should (B) Photoepolymerizationinitiater initiater under nitrogen gas stream, with 10 ℃/minute of heat-up rates when 30 ℃ are warming up to 250 ℃, the heating quality decrement is below the 15 quality %, the second-order transition temperature of the cured body that is obtained by said composition is more than 250 ℃.
2. (methyl) as claimed in claim 1 acrylic resin compsn, wherein, (A) multifunctional (methyl) propenoate accounts for more than the 90 quality % in (methyl) acrylic resin compsn.
3. according to claim 1 or claim 2 (methyl) acrylic resin compsn wherein, will be below the 6 quality % by the heating quality decrement of the resulting cured body of (methyl) acrylic resin compsn when placing 10 minutes for 300 ℃ under helium flow.
4. like each described (methyl) acrylic resin compsn in the claim 1～3, wherein,, contain (B) Photoepolymerizationinitiater initiater of 0.01～5 mass parts with respect to (A) of 100 mass parts multifunctional (methyl) propenoate.
5. like each described (methyl) acrylic resin compsn in the claim 1～4; Wherein, (B) Photoepolymerizationinitiater initiater is for being selected from 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propionyl group)-benzyl]-phenyl }-2-methyl-propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1,2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholine-4-base-phenyl)-butane-1-ketone, two (2; 4; The 6-trimethylbenzoyl) phenyl phosphine oxide, 2; 4, in 6-trimethylbenzoyl diphenyl phosphine oxide, phenylor-acetate-2-[2-oxygen-2-phenyl-acetoxyl group-oxyethyl group]-ethyl ester, phenylor-acetate 2-[2-hydroxyl-oxyethyl group]-ethyl ester more than a kind.
6. like each described (methyl) acrylic resin compsn in the claim 1～5; Wherein, (A) multifunctional (methyl) propenoate is for being selected from 1; 3-adamantyl dimethanol two (methyl) propenoate, trimethylolpropane tris (methyl) propenoate, isocyanuric acid oxyethane modification two (methyl) propenoate, isocyanuric acid oxyethane modification three (methyl) propenoate, tetramethylolmethane three (methyl) propenoate, tetramethylolmethane four (methyl) propenoate, dihydroxy methylpropane four (methyl) propenoate, Dipentaerythritol five (methyl) propenoate, Dipentaerythritol six (methyl) propenoate, 1, in 2-polyhutadiene terminal amino group manthanoate (methyl) propenoate more than a kind.
7. like each described (methyl) acrylic resin compsn in the claim 1～6, wherein, contain (C) polymerization retarder.
8. tackiness agent wherein, comprises arbitrary described (methyl) acrylic resin compsn in the claim 1～7.
9. the method for manufacture of an adherend wherein, comprising: use the described tackiness agent of claim 8 that base material is fitted, and this tackiness agent is shone visible rays or ultraviolet and base material is bonded to each other.
10. the method for use of an adherend wherein, comprising: use the described tackiness agent of claim 8 with base material fit each other, bonding after, resulting adherend is used in the environment more than 250 ℃.
11. the disassembling method of an adherend wherein, comprising: on one side to utilizing the adherend that forms after the described tackiness agent adhesive substrate of claim 8 to be heated to more than 150 ℃, Yi Bian the above light of illumination wavelength 280nm.
12. the disassembling method of adherend as claimed in claim 11, wherein, radiation source is selected from high voltage mercury lamp, ultrahigh pressure mercury lamp, metal halide lamp, xenon lamp and encloses the photoflash lamp of xenon.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009-243464 | 2009-10-22 | ||
| JP2009243464 | 2009-10-22 | ||
| PCT/JP2010/068512 WO2011049138A1 (en) | 2009-10-22 | 2010-10-20 | (meth)acrylic resin composition |
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| CN102574951A true CN102574951A (en) | 2012-07-11 |
| CN102574951B CN102574951B (en) | 2015-06-17 |
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| CN201080047821.0A Active CN102574951B (en) | 2009-10-22 | 2010-10-20 | (meth)Acrylic resin composition |
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| US (1) | US8901192B2 (en) |
| JP (1) | JP5812863B2 (en) |
| KR (1) | KR101634602B1 (en) |
| CN (1) | CN102574951B (en) |
| TW (1) | TWI495679B (en) |
| WO (1) | WO2011049138A1 (en) |
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| CN103080258A (en) * | 2010-09-01 | 2013-05-01 | 电气化学工业株式会社 | Method for disassembling bonded body, and adhesive |
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| CN104263304A (en) * | 2014-10-11 | 2015-01-07 | 瑞洲树脂（东莞）有限公司 | Photocuring filling gel and application method |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1209156A (en) * | 1996-01-11 | 1999-02-24 | 艾弗里·丹尼森公司 | Radiation-curable coating compositions |
| CN1386813A (en) * | 2001-05-18 | 2002-12-25 | 琳得科株式会社 | Pressure-sensitive adhered sheet for processing semiconductor chip |
| CN101146837A (en) * | 2005-03-18 | 2008-03-19 | 电气化学工业株式会社 | Adherent composition and method of temporarily fixing member therewith |
| CN101213225A (en) * | 2005-07-04 | 2008-07-02 | 电气化学工业株式会社 | Solidifying composition and method for temporary fixing of part by using the same |
| WO2009090922A1 (en) * | 2008-01-16 | 2009-07-23 | Hitachi Chemical Company, Ltd. | Photosensitive adhesive composition, filmy adhesive, adhesive sheet, adhesive pattern, semiconductor wafer with adhesive layer, semiconductor device, and process for producing semiconductor device |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63142040A (en) * | 1986-12-04 | 1988-06-14 | Nippon Shokubai Kagaku Kogyo Co Ltd | Coating composition and resin molded article having excellent scratch resistance and durability obtained by coating said composition |
| JP3014526B2 (en) | 1991-02-21 | 2000-02-28 | 三井化学株式会社 | Heat resistant adhesive |
| JP2718007B2 (en) * | 1995-06-06 | 1998-02-25 | 太陽インキ製造株式会社 | Alkali-developable one-pack type photo solder resist composition and method for manufacturing printed wiring board using the same |
| JP3934701B2 (en) | 1996-03-07 | 2007-06-20 | 大倉工業株式会社 | Heat resistant acrylic adhesive composition |
| ATE460204T1 (en) | 1996-09-16 | 2010-03-15 | Impulse Dynamics Nv | DEVICE FOR CONTROLLING CARDIAC OUTPUT |
| JP2000249826A (en) * | 1999-03-03 | 2000-09-14 | Jsr Corp | Radioactivity sensitive composition for color filter |
| KR100685067B1 (en) * | 2002-02-20 | 2007-02-22 | 다이니폰 인사츠 가부시키가이샤 | Resin composition and optical elements |
| JP4487473B2 (en) * | 2002-07-08 | 2010-06-23 | 日立化成工業株式会社 | Adhesive composition, adhesive film using the same, and semiconductor device using the adhesive film |
| JP4543615B2 (en) * | 2003-03-24 | 2010-09-15 | Ｄｉｃ株式会社 | Radiation curable pseudo-adhesive and laminate using the same |
| JP2004359843A (en) * | 2003-06-05 | 2004-12-24 | Nippon Shokubai Co Ltd | Actinic-radiation-curing composition |
| JP2006129678A (en) | 2004-11-01 | 2006-05-18 | Sony Corp | Power supply device |
| WO2006100788A1 (en) * | 2005-03-18 | 2006-09-28 | Denki Kagaku Kogyo Kabushiki Kaisha | Adherent composition and method of temporarily fixing member therewith |
| KR101144029B1 (en) * | 2005-05-31 | 2012-05-09 | 덴끼 가가꾸 고교 가부시키가이샤 | Energy ray-curable resin composition and adhesive using same |
| JP2006342222A (en) | 2005-06-08 | 2006-12-21 | Mitsuyoshi Sato | Light-curable resin composition |
| EP2050799B1 (en) | 2006-08-10 | 2014-06-18 | Denki Kagaku Kogyo Kabushiki Kaisha | Adhesive composition and method for temporarily fixing member by using the same |
| JP2009040924A (en) * | 2007-08-10 | 2009-02-26 | Soken Chem & Eng Co Ltd | Curable resin composition and high transparency antistatic hard coat material using the same |
-
2010
- 2010-10-20 CN CN201080047821.0A patent/CN102574951B/en active Active
- 2010-10-20 JP JP2011537285A patent/JP5812863B2/en active Active
- 2010-10-20 KR KR1020127013053A patent/KR101634602B1/en active IP Right Grant
- 2010-10-20 WO PCT/JP2010/068512 patent/WO2011049138A1/en active Application Filing
- 2010-10-20 US US13/503,546 patent/US8901192B2/en active Active
- 2010-10-22 TW TW099136113A patent/TWI495679B/en active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1209156A (en) * | 1996-01-11 | 1999-02-24 | 艾弗里·丹尼森公司 | Radiation-curable coating compositions |
| CN1386813A (en) * | 2001-05-18 | 2002-12-25 | 琳得科株式会社 | Pressure-sensitive adhered sheet for processing semiconductor chip |
| CN101146837A (en) * | 2005-03-18 | 2008-03-19 | 电气化学工业株式会社 | Adherent composition and method of temporarily fixing member therewith |
| CN101213225A (en) * | 2005-07-04 | 2008-07-02 | 电气化学工业株式会社 | Solidifying composition and method for temporary fixing of part by using the same |
| WO2009090922A1 (en) * | 2008-01-16 | 2009-07-23 | Hitachi Chemical Company, Ltd. | Photosensitive adhesive composition, filmy adhesive, adhesive sheet, adhesive pattern, semiconductor wafer with adhesive layer, semiconductor device, and process for producing semiconductor device |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103080258A (en) * | 2010-09-01 | 2013-05-01 | 电气化学工业株式会社 | Method for disassembling bonded body, and adhesive |
| CN103080258B (en) * | 2010-09-01 | 2015-01-21 | 电气化学工业株式会社 | Method for disassembling bonded body, and adhesive |
| US9067398B2 (en) | 2010-09-01 | 2015-06-30 | Denki Kagaku Kogyo Kabushiki Kaisha | Method for disassembling bonded body, and adhesive |
| CN103709942A (en) * | 2013-12-09 | 2014-04-09 | 北京国瑞升科技有限公司 | Visible light curing adhesive and preparation method thereof |
| CN104263304A (en) * | 2014-10-11 | 2015-01-07 | 瑞洲树脂（东莞）有限公司 | Photocuring filling gel and application method |
| CN104263304B (en) * | 2014-10-11 | 2016-05-11 | 瑞洲树脂（东莞）有限公司 | A kind of photocuring potting compound and application process |
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| Publication number | Publication date |
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| JPWO2011049138A1 (en) | 2013-03-14 |
| US20120205043A1 (en) | 2012-08-16 |
| TW201120123A (en) | 2011-06-16 |
| JP5812863B2 (en) | 2015-11-17 |
| KR101634602B1 (en) | 2016-06-29 |
| KR20120099053A (en) | 2012-09-06 |
| WO2011049138A1 (en) | 2011-04-28 |
| CN102574951B (en) | 2015-06-17 |
| TWI495679B (en) | 2015-08-11 |
| US8901192B2 (en) | 2014-12-02 |
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